Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]- → 4-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carbonitrile

HRID 2239288Notes

Reaction equation

HRID 2239288 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]([NH:17][C:18](=O)[CH3:19])=[C:5]([N+:21]([O-])=O)[CH:4]=1)#[N:2]>C(O)(=O)C.[Fe]>[CH3:19][C:18]1[NH:21][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[N:17]=1

Participants

4

Reactant 1

HCID 68576258Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]-

Product 1

HCID 685763664-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-{4-cyano-2-nitro-6-[(phenylmethyl)oxy]phenyl}acetamide (5.5 g, 17.7 mmol, STEP 2) and iron powder (2.96 g, 53.0 mmol) in acetic acid (90 mL) was refluxed with stirring for 2 hours. After cooling to room temperature, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuum. The residue was poured into water, and the aqueous layer was extracted with ethyl acetate/methanol (20:1). The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated in vacuum to afford the title compound as a brown solid (3.82 g, 82%).

Workup

  1. temperaturewas refluxed
  2. filtrationthe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuum
  4. additionThe residue was poured into water
  5. extractionthe aqueous layer was extracted with ethyl acetate/methanol (20:1)
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-f6d77994c6594741a2f89bc5ba23e0e1
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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